


Daddy Knows Best

by AeonFlux40



Series: Tumblr SPN Kink Bingo 2019 [1]
Category: Supernatural
Genre: Age Difference, Anal Fingering, Blow Jobs, Bottom Jack Kline, Castiel is Jack Kline's Parent, Cock Warming, Crossdressing, Daddy Kink, De-aged Jack Kline, Father/Son Incest, Gay, Hand Jobs, Incest, M/M, Pet Names, Supernatural Kink Bingo 2019, Underage - Freeform, don't forget the lube
Language: English
Status: Completed
Published: 2019-02-04
Updated: 2019-02-04
Packaged: 2019-10-22 06:49:05
Rating: Not Rated
Warnings: Underage
Chapters: 1
Words: 1,861
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17657987
Author URL: https://archiveofourown.org/users/AeonFlux40/pseuds/AeonFlux40
Summary: Castiel (30) and his son, Jack (12) were relaxing on the couch watching a movie. It was boring and Castiel was horny. He decided to have a little fun with Jack to ease up the boredom. Jack just looked so delicious and Castiel couldn’t help himself.





	Daddy Knows Best

“Hey Jack, why don’t you go put on that pretty little skirt I like?”

“Are we going to have play time?”

“Absolutely. Now do as I say and go change your clothes.”

“Yes, Daddy.”

Jack enjoyed play time with his Daddy. It started when he was eight years old. Play time mostly consisted of Jack dressing up and helping his Daddy get off. Castiel would do things to Jack too, and even put his tongue in Jack’s ass a few times. It felt weird at first, but he liked it anyway. The more they did it, the more Jack got used to it and wanted to keep doing it. The last time they played together was the first time they had sex. It was painful for Jack, and Castiel felt bad after it was over. Jack knew his Daddy didn’t mean to hurt him. He looked through his dresser, trying to find Daddy’s favorite skirt and lace panties. When Castiel started buying these clothes for Jack to wear, he was confused. He isn’t a girl, so why would his Daddy want him to dress like one? Jack went along with it because it was fun and he wanted to make his Daddy happy. After a while, he got used to the idea of dressing up and thought he looked prettier than some of the girls he knew. Jack twirled in front of his full-length mirror, admiring himself.

_Definitely prettier than the girls at school. ___

As much as Jack was confused by all of this, he didn’t see anything wrong with it either. It was normal for him. He knew deep down that he was a boy and did boy things, but this was different. Play time with his Daddy somehow freed him from the monotony of his everyday life and he was happy with it. He put on some lip gloss and went back to living room.

“That’s my good little princess.” Castiel patted his thigh. Jack walked over to him and sat on his lap, facing away from him. “You’re so beautiful.” Castiel whispered into Jack’s ear as he rubbed his thighs. “Do you have your bottle of lube?”

“No, Daddy.”

Castiel sighed. “I guess I should have told you what we were doing before you went to get dressed. I want you to sit on my cock and keep it warm for me. Understand?” Jack nodded. “Good. Now go get it so I can prep you.”

“Yes, Daddy.”

When Jack came back with his bottle of lube, Castiel told him to bend over and put his hands on the coffee table. Jack did as he was told while Castiel pulled down the lace panties. “These look so good on you, honey.” Jack whimpered when he felt his Daddy’s lips on him. Castiel spread Jack’s cheeks and licked at the small ring of muscle. He smiled as he heard the low moan from Jack’s mouth. Castiel licked and sucked as he squeezed Jack’s ass. He enjoyed eating out Jack and was pleasantly surprised when Jack said he enjoyed it just as much. He reached for the bottle of lube and squirted some on his finger.

“Daddy, that’s cold.” Jack gasped when Castiel circled his hole with his lubed finger.

“Shhh, it’s okay, sweetheart.” Castiel rubbed Jack’s back to soothe him. This part of their play time was still new for Jack. Castiel wanted to wait until Jack felt he was ready. He worked in one finger slowly. Jack grimaced and clenched around Castiel’s finger.

“Daddy...”

“Try to relax, Jack. I have to do this properly.” Castiel continued. “Remember last time?” Jack nodded. He remembered. It hurt so much, and he really didn’t want it to be that bad again. Better listen to his Daddy and do this right. Jack did his best to relax and let Castiel take care of him. After all, Daddy knows best. He breathed in and out slowly, concentrating on keeping his body lax, allowing Castiel to do what he needed. “That’s it, princess. Just relax. You’re doing so good.” Jack preened at his father’s words. It made him feel good inside knowing that he was making him happy. “Okay, Jack. I’m gonna put in another finger. Are you ready?”

“Yes, Daddy.”

Jack groaned as Castiel inserted a second finger. Slowly, he pushed his fingers in and drew them out. Castiel’s dick was rock hard in his pants. He wanted so very much to be inside his boy but knew that he had to take his time lubing him up first. They had only done this once and the first time wasn’t a very good experience for Jack. He didn’t want a repeat of that, and he had to make sure Jack was ready this time. “You doing okay, sweetheart?”

“Yes, Daddy. I’m good.”

Castiel continued fingering Jack. His princess was so hot and warm, he couldn’t wait to get inside. Jack whimpered when Castiel’s fingers brushed over that soft spot he was trying to find. Castiel chuckled. He rubbed over that spot a couple of times, making Jack squirm. He reached around and felt how hard Jack’s dick was. “Mmmm, princess. Does that feel good?” Jack nodded furiously. He moved his hips back and forth, fucking himself on his Daddy’s big fingers. Castiel stroked him, causing his boy to moan loudly.

“Daddy…so good. Please don’t stop.”

Castiel chuckled. “Of course not, Princess. I’m gonna add another finger, okay?” Jack nodded. He had no idea play time could be this incredible. He was so thankful that his Daddy was patient with him. It all felt so good. Jack could feel the heat growing in his belly. Castiel felt as his boy clenched around his fingers and came all over his hand. He continued fingering and stroking Jack, working him through his orgasm. Jack moaned over and over as his Daddy rubbed that spot inside of him without mercy. He cried out as another wave of orgasm hit him. He wanted the feeling to last forever, but he was starting to hurt from all the stimulation.

“Please, Daddy. I can’t take anymore. It hurts.”

Castiel removed his fingers and pulled Jack onto his lap holding him close. “Such a good little princess.” He whispered, kissing Jack on his neck. “Always so good for Daddy.” Jack was still trembling a little bit. Castiel held him and soothed him, making sure he was okay. “Stay here and I’ll go get something to clean you up.” Jack nodded and sat back on the couch. His skirt and thighs were sticky with his cum. Castiel returned with a warm washcloth and wiped him down. After he was finished, Castiel stood up and removed his pants. Jack could see his hard cock tenting his briefs. He reached out for Castiel and pulled him close. “You wanna suck Daddy’s cock, princess?”

“Please. Can I?”

Castiel nodded. Jack smiled as he pulled out his Daddy’s dick and went down on him. He loved sucking off his Daddy. He loved the way his Daddy praised him, and when he pulled on Jack’s hair when he was about to come. Jack remembered everything his Daddy taught him and put his mouth to good use. Castiel moaned. “God, Jack. Your mouth is so amazing.” He really wanted to come down Jack’s throat, but that wasn’t in his plan for the night. Castiel tapped gently on the side of Jack’s face and he stopped, looking up at his Daddy. “You’re so beautiful like this, sweetheart.” Castiel pulled Jack to his feet and kissed him. He could taste himself on Jack’s tongue and he loved it. Castiel sat down on the couch and lubed his cock. It was starting to ache a bit from not having release, but he wanted to wait until he was inside Jack. He motioned for Jack to turn around. Castiel pulled Jack’s cheeks apart and tugged him closer until he was hovering over Castiel’s dick. “I’m gonna go slow, princess. Tell me if it gets to be too much, okay?”

“Okay, Daddy.”

Castiel lined himself up with Jack’s hole and slowly pushed in. He was able to push the head of his penis inside before Jack told him to stop. “I just need a minute to adjust, Daddy.” Castiel waited until Jack was ready, and slowly pulled him down. Inch by inch, Castiel went deeper and deeper into his precious little boy. The tightness and warmth almost had him coming right away, but he was able to hold off. When Jack was fully seated in Castiel’s lap, he pulled him against his chest. “You okay, baby?” Jack nodded. Castiel ran his fingers through Jack’s hair, kissing gently on his neck. “Mmmm. Feels so amazing to be inside you, princess. You’re so good for me.”

“Thank you, Daddy.”

“Let’s watch a movie. Try to sit still, honey. Just keep Daddy’s cock warm, okay? Can you do that?”

“I’ll try.”

Castiel flipped through Netflix and found a movie for them to watch. He was glad Jack was so comfortable sitting on his dick. It would make it easier for when he wanted to fuck him. He wasn’t as gentle before, and he regretted that. This is what he should have done. Castiel loves his son and would never do anything to hurt him on purpose. He reached under Jack’s skirt and rubbed his thighs. Jack hadn’t hit puberty just yet, so his skin was silky smooth and hairless. Castiel loved that about him. He rubbed circles on Jack’s thighs, smiling as the boy sighed and relaxed in his lap. He moved his hand further up and gently cupped Jack’s cock and balls. Jack whimpered. Castiel’s other hand went under Jack’s shirt, playing with his nipple.

“Daddy…” Jack whined. He wanted to rut against his Daddy’s hand but didn’t because he promised he wouldn’t move. Castiel smiled as he watched his boy struggle with trying to sit still. It was adorable. He pinched Jack’s nipple, producing a small whimper from him. Jack’s dick was hard again from all the touching. Castiel couldn’t help himself, he loved touching Jack. He loved the way Jack responded to him, it turned him on. Castiel stroked Jack’s cock, rubbing his thumb over the head and playing with his slit. Jack squirmed in his Daddy’s lap. There was so much sensation, it was overwhelming.

“Come for me, princess. I wanna know what it feels like to be inside you when you come.”

Jack let out a loud moan as Castiel bit down on the nape of his neck. He came all over his Daddy’s hand again. Castiel groaned and spilled inside of his boy, the feeling of Jack’s orgasm sending him over the edge himself. He rocked his hips back and forth slowly, enjoying the feeling of still being inside of Jack. Castiel lay his head against Jack, breathing heavily and waiting for his head to stop spinning.

“Daddy, are you okay?”

“Yes, Jack. Daddy’s alright. How about you? Are you good?”

Jack nodded. He loved it when his Daddy held him close after play time. It was very comforting. He grabbed Castiel’s hand and kissed it.

“I love you, Daddy.”

**Author's Note:**

> SPN Kink Bingo square filled: Cockwarming. I hope y'all enjoyed reading.


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